Convenient Syntheses of Chiral Cyclic Sulfinates (Sultines) from Unsaturated Alcohols

Article abstract of DOI:10.1021/jo00129a056

The reaction of unsaturated alcohols with N-sulfinyl-p-toluenesulfonamide (TsNSO) is shown to lead stereoselectively to chiral cyclic or bicyclic sulfinates (sultines).The reactions occur at ambient temperatures and afford a general route to δ and ε-sultines which are notable for their crystallinity and thermal stability.These studies confirm the preservation of stereochemical integrity of the carbon atom α to the oxygen atom in the sultine ring.Some unsaturated aldehydes furnish sultines via a tandem oxo-ene cyclization and subsequent ring closure to the sultine.In some reactions, N-toluenesulfonamide derivatives of sultines (compounds of type 11) were isolated, and since those were converted into the sultines by the action of BF3*OEt2, such sulfonamides are considered to be intermediates in the reaction pathway.